CA2568159A1 - Tetrahydro-imidazo [1,5-a] pyridin derivatives as aldosterone synthase inhibitors - Google Patents
Tetrahydro-imidazo [1,5-a] pyridin derivatives as aldosterone synthase inhibitors Download PDFInfo
- Publication number
- CA2568159A1 CA2568159A1 CA002568159A CA2568159A CA2568159A1 CA 2568159 A1 CA2568159 A1 CA 2568159A1 CA 002568159 A CA002568159 A CA 002568159A CA 2568159 A CA2568159 A CA 2568159A CA 2568159 A1 CA2568159 A1 CA 2568159A1
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- Prior art keywords
- alkyl
- compound
- aryl
- general formula
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 229940123338 Aldosterone synthase inhibitor Drugs 0.000 title abstract description 4
- KMJZZOUSHSRQSL-UHFFFAOYSA-N 1,2,3,5-tetrahydroimidazo[1,5-a]pyridine Chemical class C1=CCN2CNCC2=C1 KMJZZOUSHSRQSL-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 100
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000003814 drug Substances 0.000 claims abstract 4
- -1 di-substituted benzofuranyl Chemical group 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 30
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229960000890 hydrocortisone Drugs 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 210000004369 blood Anatomy 0.000 claims description 8
- 239000008280 blood Substances 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 241000282414 Homo sapiens Species 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 201000009395 primary hyperaldosteronism Diseases 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 230000000297 inotrophic effect Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 229940127557 pharmaceutical product Drugs 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 230000002503 metabolic effect Effects 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 9
- 230000001575 pathological effect Effects 0.000 claims 4
- 206010020571 Hyperaldosteronism Diseases 0.000 claims 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 7
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 241001465754 Metazoa Species 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
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- 239000000126 substance Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- KCWZGJVSDFYRIX-YFKPBYRVSA-N N(gamma)-nitro-L-arginine methyl ester Chemical compound COC(=O)[C@@H](N)CCCN=C(N)N[N+]([O-])=O KCWZGJVSDFYRIX-YFKPBYRVSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 7
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
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- 241000700159 Rattus Species 0.000 description 7
- 229960002478 aldosterone Drugs 0.000 description 7
- 238000002405 diagnostic procedure Methods 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- 101800000733 Angiotensin-2 Proteins 0.000 description 6
- 102400000345 Angiotensin-2 Human genes 0.000 description 6
- 206010020772 Hypertension Diseases 0.000 description 6
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229950006323 angiotensin ii Drugs 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
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- SPZRVKIZAPHPOR-UHFFFAOYSA-N 6,7-dihydro-5h-imidazo[1,5-a]pyridin-8-one Chemical compound O=C1CCCN2C=NC=C12 SPZRVKIZAPHPOR-UHFFFAOYSA-N 0.000 description 4
- 102000014654 Aromatase Human genes 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
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Classifications
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- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
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- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
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- Animal Behavior & Ethology (AREA)
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- Diabetes (AREA)
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- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
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- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH9152004 | 2004-05-28 | ||
| CH915/04 | 2004-05-28 | ||
| PCT/EP2005/052419 WO2005118581A1 (en) | 2004-05-28 | 2005-05-27 | Tetrahydro-imidazo [1,5-a] pyridin derivatives as aldosterone synthase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2568159A1 true CA2568159A1 (en) | 2005-12-15 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
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| CA002568159A Abandoned CA2568159A1 (en) | 2004-05-28 | 2005-05-27 | Tetrahydro-imidazo [1,5-a] pyridin derivatives as aldosterone synthase inhibitors |
| CA002568163A Abandoned CA2568163A1 (en) | 2004-05-28 | 2005-05-27 | Bicyclic, nitrogen-containing heterocycles as aromatase inhibitors |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002568163A Abandoned CA2568163A1 (en) | 2004-05-28 | 2005-05-27 | Bicyclic, nitrogen-containing heterocycles as aromatase inhibitors |
Country Status (10)
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| AR (2) | AR049125A1 (enExample) |
| BR (2) | BRPI0511621A (enExample) |
| CA (2) | CA2568159A1 (enExample) |
| IL (2) | IL179408A0 (enExample) |
| TW (2) | TW200616623A (enExample) |
| WO (2) | WO2005118540A2 (enExample) |
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| WO2006005725A2 (en) * | 2004-07-09 | 2006-01-19 | Speedel Experimenta Ag | N containing condensed heterocycles with antitumor effects |
| AR056888A1 (es) * | 2005-12-09 | 2007-10-31 | Speedel Experimenta Ag | Derivados de heterociclil imidazol |
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| EP1842543A1 (en) | 2006-04-05 | 2007-10-10 | Speedel Pharma AG | Pharmaceutical composition coprising an aldosterone synthase inhibitor and a mineralcorticoid receptor antagonist |
| TW200808812A (en) * | 2006-04-12 | 2008-02-16 | Speedel Experimenta Ag | Imidazo compounds |
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| TW200808813A (en) * | 2006-04-12 | 2008-02-16 | Speedel Experimenta Ag | Imidazo compounds |
| BRPI0916355B8 (pt) * | 2008-07-24 | 2022-12-13 | Meiji Seika Kaisha | Vetor recombinante compreendendo um polinucleotídeo isolado, e, método para produzir um precursor de piripiropeno a |
| WO2010052445A1 (en) * | 2008-11-07 | 2010-05-14 | University Of Sheffield | Medicament and method of diagnosis |
| CN104370932A (zh) | 2009-05-13 | 2015-02-25 | 明治制果药业株式会社 | 生产啶南平衍生物的方法 |
| ES2602826T3 (es) | 2009-05-28 | 2017-02-22 | Novartis Ag | Derivados aminobutíricos sustituidos como inhibidores de neprilisina |
| CN102448928B (zh) | 2009-05-28 | 2014-10-01 | 诺华股份有限公司 | 作为中性溶酶(neprilysin)抑制剂的取代的氨基丁酸衍生物 |
| EP2501678B1 (en) * | 2009-11-17 | 2015-09-23 | Novartis AG | Aryl-pyridine derivatives as aldosterone synthase inhibitors |
| JO2967B1 (en) | 2009-11-20 | 2016-03-15 | نوفارتس ايه جي | Acetic acid derivatives of carbamoyl methyl amino are substituted as new NEP inhibitors |
| UA111151C2 (uk) | 2010-03-01 | 2016-04-11 | Мейдзі Сейка Фарма Ко., Лтд. | Спосіб одержання похідних пірипіропену |
| US8877815B2 (en) | 2010-11-16 | 2014-11-04 | Novartis Ag | Substituted carbamoylcycloalkyl acetic acid derivatives as NEP |
| US8673974B2 (en) | 2010-11-16 | 2014-03-18 | Novartis Ag | Substituted amino bisphenyl pentanoic acid derivatives as NEP inhibitors |
| RU2609200C2 (ru) | 2011-07-08 | 2017-01-30 | Новартис Аг | Способ лечения атеросклероза у субъектов с высоким уровнем триглицеридов |
| CN103958478B (zh) * | 2011-11-30 | 2017-08-01 | 霍夫曼-拉罗奇有限公司 | 双环二氢异喹啉‑1‑酮衍生物 |
| UY35144A (es) | 2012-11-20 | 2014-06-30 | Novartis Ag | Miméticos lineales sintéticos de apelina para el tratamiento de insuficiencia cardiaca |
| SG11201506018PA (en) | 2013-02-14 | 2015-08-28 | Novartis Ag | Substituted bisphenyl butanoic phosphonic acid derivatives as nep (neutral endopeptidase) inhibitors |
| TW201536814A (zh) | 2013-07-25 | 2015-10-01 | Novartis Ag | 用於治療心臟衰竭之合成環狀多肽 |
| TW201518323A (zh) | 2013-07-25 | 2015-05-16 | Novartis Ag | 合成ａｐｅｌｉｎ多肽之生物結合物 |
| WO2015055602A1 (en) * | 2013-10-17 | 2015-04-23 | F. Hoffmann-La Roche Ag | Phenyl-dihydropyridine derivatives as inhibitors of aldosterone synthase |
| CN105593212B (zh) * | 2013-10-17 | 2019-06-04 | 豪夫迈·罗氏有限公司 | 作为醛固酮合酶抑制剂的苯基-二氢吡啶衍生物 |
| RU2016116433A (ru) * | 2013-10-17 | 2017-11-22 | Ф. Хоффманн-Ля Рош Аг | Новые производные фенил-дигидропиридина в качестве ингибиторов альдостерон синтазы |
| CA2972871A1 (en) | 2015-01-23 | 2016-07-28 | Novartis Ag | Synthetic apelin fatty acid conjugates with improved half-life |
| JOP20190086A1 (ar) | 2016-10-21 | 2019-04-18 | Novartis Ag | مشتقات نافثيريدينون جديدة واستخدامها في معالجة عدم انتظام ضربات القلب |
| CN110582278B (zh) | 2017-03-10 | 2023-04-18 | 伊姆贝拉神经疗法公司 | 药物组合物及其用途 |
| UY38072A (es) | 2018-02-07 | 2019-10-01 | Novartis Ag | Compuestos derivados de éster butanoico sustituido con bisfenilo como inhibidores de nep, composiciones y combinaciones de los mismos |
| WO2020110008A1 (en) | 2018-11-27 | 2020-06-04 | Novartis Ag | Cyclic pentamer compounds as proprotein convertase subtilisin/kexin type 9 (pcsk9) inhibitors for the treatment of metabolic disorder |
| JP7657151B2 (ja) | 2018-11-27 | 2025-04-04 | ノバルティス アーゲー | 代謝性障害の処置のためのプロタンパク質コンバターゼスブチリシン／ケキシン９型（ｐｃｓｋ９）阻害剤としての環状ペプチド |
| UY38485A (es) | 2018-11-27 | 2020-06-30 | Novartis Ag | Compuestos tetrámeros cíclicos como inhibidores de proproteína convertasa subtilisina/kexina tipo 9 (pcsk9), método de tratamiento, uso y su preparación |
| WO2023084449A1 (en) | 2021-11-12 | 2023-05-19 | Novartis Ag | Diaminocyclopentylpyridine derivatives for the treatment of a disease or disorder |
| AR127698A1 (es) | 2021-11-23 | 2024-02-21 | Novartis Ag | Derivados de naftiridinona para el tratamiento de una enfermedad o un trastorno |
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| CN117659075B (zh) * | 2023-12-18 | 2025-02-11 | 中国科学院兰州化学物理研究所 | 一种咪唑衍生型柱[5]芳烃手性填料的制备及应用 |
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| US4617307A (en) * | 1984-06-20 | 1986-10-14 | Ciba-Geigy Corporation | Substituted imidazo[1,5-A]pyridine derivatives as aromatase inhibitors |
| US4889861A (en) * | 1982-12-21 | 1989-12-26 | Ciba-Geigy Corp. | Substituted imidazo[1,5-a]pyridine derivatives and other substituted bicyclic derivatives and their use as aromatase inhibitors |
| JPH0670064B2 (ja) | 1986-12-08 | 1994-09-07 | 三井石油化学工業株式会社 | 二環性イミダゾ−ル誘導体 |
| GB8820730D0 (en) * | 1988-09-02 | 1988-10-05 | Erba Carlo Spa | Substituted 5 6 7 8-tetrahydroimidazo/1.5-a/pyridines & process for their preparation |
| US5057521A (en) | 1988-10-26 | 1991-10-15 | Ciba-Geigy Corporation | Use of bicyclic imidazole compounds for the treatment of hyperaldosteronism |
| CA2026792A1 (en) * | 1989-11-01 | 1991-05-02 | Michael N. Greco | (6,7-dihydro-5h-pyrrolo[1,2-c]imidazol-5-yl)- and (5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl) substituted 1h-benzotriazole derivatives |
| JPH07503242A (ja) * | 1992-01-27 | 1995-04-06 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | アロマターゼ阻害剤としてのピロロイミダゾリルおよびイミダゾピリジニル置換１ｈ−ベンズイミダゾール誘導体 |
| US5763611A (en) * | 1992-05-29 | 1998-06-09 | The Procter & Gamble Company | Thio-substituted cyclic phosphonate compounds, pharmaceutical compositions, and methods for treating abnormal calcium and phosphate metabolism |
| AU6015796A (en) * | 1995-06-14 | 1997-01-15 | Yamanouchi Pharmaceutical Co., Ltd. | Fused imidazole derivatives and medicinal composition thereof |
| JPH0971586A (ja) * | 1995-09-07 | 1997-03-18 | Yamanouchi Pharmaceut Co Ltd | 新規な二環性縮合イミダゾール誘導体 |
| US6333335B1 (en) * | 1999-07-23 | 2001-12-25 | Merck & Co., Inc. | Phenyl-protein transferase inhibitors |
| JP2001151696A (ja) * | 1999-11-22 | 2001-06-05 | Keiko Tanaka | アクチニジンから造る腫瘍の増殖ならびに転移抑制酵素と異質なたんぱく細胞の除去剤 |
| KR100725442B1 (ko) * | 2000-11-17 | 2007-06-07 | 다케다 야쿠힌 고교 가부시키가이샤 | 신규 이미다졸 유도체, 이의 제조 방법 및 이의 용도 |
| US20080076794A1 (en) * | 2004-05-28 | 2008-03-27 | Peter Herold | Heterocyclic Compounds And Their Use As Aldosterone Synthase Inhibitors |
| TW200616623A (en) * | 2004-05-28 | 2006-06-01 | Speedel Experimenta Ag | Organic compounds |
| JP2008500998A (ja) * | 2004-05-28 | 2008-01-17 | シュペーデル・エクスペリメンタ・アーゲー | 複素環式化合物およびアルドステロンシンターゼ阻害薬としてのそれらの使用 |
| TW200716105A (en) * | 2005-05-31 | 2007-05-01 | Speedel Experimenta Ag | Imidazole compounds |
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2006
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- 2006-11-20 IL IL179406A patent/IL179406A0/en unknown
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| Publication number | Publication date |
|---|---|
| CA2568163A1 (en) | 2005-12-15 |
| IL179406A0 (en) | 2007-05-15 |
| WO2005118581A1 (en) | 2005-12-15 |
| JP2008500997A (ja) | 2008-01-17 |
| TW200612947A (en) | 2006-05-01 |
| JP5179174B2 (ja) | 2013-04-10 |
| JP2008501000A (ja) | 2008-01-17 |
| IL179408A0 (en) | 2007-05-15 |
| US8680079B2 (en) | 2014-03-25 |
| US20080076784A1 (en) | 2008-03-27 |
| CN1960991A (zh) | 2007-05-09 |
| AR049126A1 (es) | 2006-06-28 |
| CN1968930A (zh) | 2007-05-23 |
| BRPI0511621A (pt) | 2008-01-02 |
| TW200616623A (en) | 2006-06-01 |
| US20070225232A1 (en) | 2007-09-27 |
| WO2005118540A3 (en) | 2006-02-02 |
| BRPI0510409A (pt) | 2007-10-23 |
| EP1749005A1 (en) | 2007-02-07 |
| EP1765777A2 (en) | 2007-03-28 |
| AR049125A1 (es) | 2006-06-28 |
| WO2005118540A2 (en) | 2005-12-15 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20130226 |